organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1H-Benzimidazole-2(3H)-thione

aState Key Laboratory of Materials-Oriented Chemical Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and bCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
*Correspondence e-mail: dcwang@njut.edu.cn

(Received 27 February 2009; accepted 5 March 2009; online 14 March 2009)

The asymmetric unit of the title compound, C7H6N2S, contains one half-mol­ecule; the C and S atoms of the C=S group lie on a crystallographic mirror plane. In the crystal structure, inter­molecular N—H⋯S hydrogen bonds link the mol­ecules.

Related literature

For a related structure, see: Mavrova et al. (2007[Mavrova, A. Ts., Denkova, P., Tsenov, Y. A., Anichina, K. K. & Vutchev, D. I. (2007). Bioorg. Med. Chem. 15, 6291-6297.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C7H6N2S

  • Mr = 150.21

  • Monoclinic, P 21 /m

  • a = 4.915 (1) Å

  • b = 8.5590 (17) Å

  • c = 8.2920 (17) Å

  • β = 91.76 (3)°

  • V = 348.66 (12) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.38 mm−1

  • T = 294 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.896, Tmax = 0.963

  • 903 measured reflections

  • 813 independent reflections

  • 647 reflections with I > 2σ(I)

  • Rint = 0.044

  • 3 standard reflections frequency: 120 min intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.152

  • S = 1.00

  • 813 reflections

  • 45 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N—H0A⋯Si 0.86 2.57 3.3798 (19) 158
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+2].

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

It is a kind of secondary age inhibitor, and could reinforce the effect combined with DNP AP and other nonpolluting age inhibitors. It disperses easily in rubber, and the color does not change under sun exposure. Its pollution capacity is limited. 2-Mercaptobenzimidiazole is a new kind of anti-leprosy drugs, and its toxicity is lower than sulphone drugs. It should not be used in the patients to which can not be given sulphone drugs. We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains one-half molecule, in which a mirror plane passes through S and C4 atoms. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal structure, intermolecular N-H···S hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For a related structure, see: Mavrova et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title comppund, 1,2-diaminobenzene (0.019 mol) and water (3 ml) were added to a solution of sodium hydroxide (0.022 mol) in ethanol (20 ml) and carbon disulfide (0.022 mol). The mixture was heated under reflux for 3 h. Charcoal was added cautiously and removed by filtration after the mixture has been refluxed for 10 min more. The filtrate was heated to 377 K and quenched with warm water (377 K, 20 ml), and then acetic acid (9 ml) was added by stirring. The product was separated and after cooling in refrigerator for 3 h the crystallization was completed (Mavrova et al., 2007). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution after two weeks.

Refinement top

H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 Å for aromatic H and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.
1H-Benzimidazole-2(3H)-thione top
Crystal data top
C7H6N2SF(000) = 156
Mr = 150.21Dx = 1.431 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 25 reflections
a = 4.915 (1) Åθ = 10–14°
b = 8.5590 (17) ŵ = 0.38 mm1
c = 8.2920 (17) ÅT = 294 K
β = 91.76 (3)°Block, colorless
V = 348.66 (12) Å30.30 × 0.20 × 0.10 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
647 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 27.0°, θmin = 2.5°
ω/2θ scansh = 06
Absorption correction: ψ scan
(North et al., 1968)
k = 010
Tmin = 0.896, Tmax = 0.963l = 1010
903 measured reflections3 standard reflections every 120 min
813 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1P)2 + 0.059P]
where P = (Fo2 + 2Fc2)/3
813 reflections(Δ/σ)max < 0.001
45 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C7H6N2SV = 348.66 (12) Å3
Mr = 150.21Z = 2
Monoclinic, P21/mMo Kα radiation
a = 4.915 (1) ŵ = 0.38 mm1
b = 8.5590 (17) ÅT = 294 K
c = 8.2920 (17) Å0.30 × 0.20 × 0.10 mm
β = 91.76 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
647 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.044
Tmin = 0.896, Tmax = 0.9633 standard reflections every 120 min
903 measured reflections intensity decay: 1%
813 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.00Δρmax = 0.37 e Å3
813 reflectionsΔρmin = 0.26 e Å3
45 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.06322 (19)0.25000.88609 (10)0.0510 (3)
N0.2841 (4)0.1239 (2)1.1022 (2)0.0465 (5)
H0A0.25050.02811.07830.056*
C10.7826 (5)0.1687 (4)1.4250 (3)0.0644 (7)
H1A0.89140.11541.49640.077*
C20.6229 (5)0.0844 (3)1.3201 (3)0.0561 (7)
H2A0.62430.02421.31950.067*
C30.4611 (4)0.1684 (3)1.2162 (3)0.0437 (5)
C40.1646 (7)0.25001.0292 (4)0.047
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0671 (6)0.0270 (5)0.0588 (6)0.0000.0015 (4)0.000
N0.0585 (11)0.0227 (9)0.0578 (12)0.0010 (8)0.0061 (9)0.0009 (8)
C10.0621 (14)0.0558 (17)0.0755 (18)0.0084 (13)0.0082 (13)0.0065 (14)
C20.0681 (15)0.0359 (13)0.0640 (16)0.0047 (12)0.0032 (13)0.0047 (11)
C30.0484 (11)0.0302 (12)0.0519 (13)0.0009 (9)0.0094 (9)0.0003 (9)
C40.0570.0290.0540.0000.0190.000
Geometric parameters (Å, º) top
S—C41.656 (4)C1—H1A0.9300
N—C31.359 (3)C2—C31.390 (3)
N—C41.378 (3)C2—H2A0.9300
N—H0A0.8600C3—C3i1.398 (4)
C1—C21.391 (4)C4—Ni1.378 (3)
C1—C1i1.391 (6)
C3—N—C4112.1 (2)C1—C2—H2A121.2
C3—N—H0A123.9N—C3—C2132.6 (2)
C4—N—H0A123.9N—C3—C3i106.27 (12)
C2—C1—C1i121.24 (16)C2—C3—C3i121.11 (15)
C2—C1—H1A119.4N—C4—Ni103.2 (3)
C1i—C1—H1A119.4N—C4—S128.40 (15)
C3—C2—C1117.6 (2)Ni—C4—S128.40 (15)
C3—C2—H2A121.2
C1i—C1—C2—C30.6 (3)C1—C2—C3—C3i0.6 (3)
C4—N—C3—C2179.1 (2)C3—N—C4—Ni1.5 (3)
C4—N—C3—C3i1.0 (2)C3—N—C4—S179.5 (2)
C1—C2—C3—N179.5 (2)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H0A···Sii0.862.573.3798 (19)158
Symmetry code: (ii) x, y1/2, z+2.

Experimental details

Crystal data
Chemical formulaC7H6N2S
Mr150.21
Crystal system, space groupMonoclinic, P21/m
Temperature (K)294
a, b, c (Å)4.915 (1), 8.5590 (17), 8.2920 (17)
β (°) 91.76 (3)
V3)348.66 (12)
Z2
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.896, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
903, 813, 647
Rint0.044
(sin θ/λ)max1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.152, 1.00
No. of reflections813
No. of parameters45
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.26

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H0A···Si0.862.573.3798 (19)158.00
Symmetry code: (i) x, y1/2, z+2.
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationMavrova, A. Ts., Denkova, P., Tsenov, Y. A., Anichina, K. K. & Vutchev, D. I. (2007). Bioorg. Med. Chem. 15, 6291–6297.  Web of Science CrossRef PubMed CAS Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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